Bob Dylan's Five Best Songs More Than 10 Minutes Long

Bob Dylan has no trouble with brevity. Some of the rock legend's best-received albums, like 1969’s Nashville Skyline or 2015’s Shadows In the Night, feature tracklists that scarcely breach four minutes, which the latter does exactly once. But then there’s the other Dylan — the fearless bard whose verses full of obscure references, romantic dilemmas and sketchy characters start piling up, and suddenly ten minutes have gone by and the song still isn’t over.

Given how tightly the sets are spaced together, those types of songs may not show up at "Thanks Bob 2017," tomorrow afternoon’s KPFT-sponsored Dylan tribute at Bubba’s Bar & Grill on Washington. Just a hunch, but the likes of “Subterranean Homesick Blues,” “All Along the Watchtower” or “You Ain’t Goin’ Nowhere,” all of them a punkish three minutes or less, may be more this show’s speed. Luckily the program sponsoring the benefit, DeadBeat, has never been shy about spinning Dylan’s more extended compositions. To us, the songs that stretch over the length of two or three regular songs are truly Dylan at his Dylan-est.

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5. "Joey" Running Time: 11:05 Album:Desire (1976)

“Joey” is very few people’s idea of top-shelf Dylan, except perhaps Dylan himself. Back in the day, he took quite a bit of heat for recording this tribute (if that’s even the right word) to New York mobster “Crazy” Joe Gallo, who was gunned down while eating out on his birthday in 1972. Legendary rock critic Lester Bangs certainly raked Dylan over the coals, calling the song “one of the most mindlessly amoral pieces of repellent romanticist bullshit ever recorded.” Its placement on the same album as “Hurricane,” Dylan’s hit song about wrongfully imprisoned boxing champ Rubin “Hurricane” Carter, makes it that much more perplexing. Questionable though Dylan’s judgement may be, however, his choice of collaborator is not. Written by Broadway lyricist Jacques Levy (Oh! Calcutta!), lines like “He pushed the table over to protect his family/ Then staggered out into the streets of Little Italy” sound lifted straight out of some pulpy ‘70s NYC tabloid.

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4. "Highlands" Running Time: 16:32 Album:Time Out of Mind (1997)

Rambling at a snail’s pace, “Highlands” closes Dylan’s Album of the Year Grammy winner, and ranks as his longest recorded song to date. The lyrics cut between the narrator’s imagination (the song is reportedly based on Robert Burns’ 1789 poem “My Heart’s In the Highlands”) and a real world that piles on one disappointment after another. There is wisdom here, of the weary variety — “Every day is the same thing out the door/ Feel further away than ever before” — and more than a few non-sequiturs within its 20 verses. Seven alone are consumed by Dylan’s conversation with a waitress he meets in a Boston diner; the rest pretty much amount to a fire sale on whatever random thoughts happen to cross his mind as it drifts back to those fields near Aberdeen. Best: “I think what I need might be a full-length leather coat/ Somebody just asked me if I registered to vote.”

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3. "Tempest" Running Time: 13:55 Album:Tempest (2012)

Released the centennial year of the Titanic’s sinking, Dylan’s longest recorded song this decade recounts the event in as much detail as nearly a quarter of an hour will allow — even a few allusions to James Cameron’s Oscar-winning 1997 film. The North Atlantic disaster shook Western society’s faith in the progress represented by technological developments like enormous ocean liners, and provides plenty of food for thought for the sharps over at genius.com a century later. Dylan using one of the ship’s watchman as an anchor (pardon the pun) leads one commentator to see a link to the Old Testament book of Ezekiel — which Dylan mentions in several other songs throughout Tempest — while another detects an unsettling parallel to the present day: “One could take the whole song as an accurate description of what is happening in the world: bad things taking place, but people are either oblivious or unable to act.”

‘80s Dylan has its defenders, not least the artists appearing on ATO Records’ 2014 compilationBob Dylan In the ‘80s, Volume One: A Tribute to ‘80s Dylan. (Got all that?) That said, it’s hard to find people willing to say many nice things about Knocked Out Loaded, with the possible exception of “Brownsville Girl.” Dylan and actor/playwright Sam Shepherd’s collaboration scans exactly like a script Shepherd might have written and a song Dylan might have recorded in the mid-‘80s: the arrangement is loaded with horns, female vocals, and lots of echo, while the plot concerns half-remembered Gregory Peck movies and old lovers who once raised a good bit of hell across the Southwest. Still, the real ache in Dylan's voice makes "Brownsville Girl" oddly endearing; besides, there's the Texas borderlands setting and this possible cry for help: “If there’s an original thought out there, I could use it right now.” Enter the Traveling Wilburys…

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Dylan’s sixth album and arguably his first full-on “rock” LP, Highway 61 Revisited looms about as large in popular music today as it did upon its release in 1965, and “Desolation Row” remains both crown jewel and acoustic outlier. Eleven and a half minutes of poignant Spanish-style guitar and heartbreaking harmonica, it’s almost Rashomon-like in its invitation to interpretation: Some see a relatively simple parable of America’s social upheaval during the ‘60s, others an intricately woven tapestry of literary, Biblical and cultural allusions. Perhaps it’s just a restless guy in his mid-twenties, an acknowledged fan of Allen Ginsberg and John Steinbeck, coming to grips with his new life as one of the most famous people in New York City the best way he knows how. Only Dylan himself knows what secrets are really hiding in those lyrics, and he’s not telling. But if any one of his early songs predicts a career that would yield a Nobel Prize for Literature a half-century later, it’s this one.